3-((2S,5S)-4-methylene-5-(3-oxopropyl)tetrahydrofuran-2-yl)propanol derivatives have the structure of the following formula (1), and have been effectively used as intermediates for C14-C23 moiety in the preparation of Halichondrin B of the following formula (2) and Eribulin mesylate of the following formula (3) having anti-cancer activity[see U.S. Pat. No. 5,436,238 and Korean Patent No. 10-1434673].

For the preparation of the 3-((2S,5S)-4-methylene-5-(3-oxopropyl)tetrahydrofuran-2-yl)propanol derivatives of formula (1), various synthesis processes have been reported, but most of them have problems of an excessively long synthetic pathway and low yields.
For example, the preparation process disclosed in Korean Patent No. 10-1434673 includes ozonolysis, hydrogenation, and repeated protections and deprotections, so it is inefficient and has long reaction steps, thereby being difficult to be industrialized.
Further, Wo2014/183211A1 discloses that the 3-((2S,5S)-4-methylene-5-(3-oxopropyl)tetrahydrofuran-2-yl)propanol derivatives of formula (1) can be prepared through the synthetic steps of the following Reaction Scheme 1.

However, compound 6a produced in Reaction Scheme 1 is difficult to be separated because an epimer is formed due to low stereoselectivity in position 2 of the furan ring.
Therefore, there has been a need to develop a process capable of preparing the 3-((2S,5S)-4-methylene-5-(3-oxopropyl)tetrahydrofuran-2-yl)propanol derivatives of formula (1) by a simple process with high yields.